Herbicidal or fungicidal sulphonylaminocarbonyltriazolinones with halogenated alk(en)oxy substituents

ABSTRACT

The invention relates to novel sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents of the formula (I) ##STR1## in which R 1  represents hydrogen, hydroxyl, amino, alkylideneamino or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, 
     R 2  represents respectively halogen-substituted alkyl or alkenyl, and 
     R 3  represents a respectively optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl, 
     and salts of compounds of the formula (I), and to processes and novel intermediates for preparing the compounds (I), and to their use as herbicides and/or fungicides.

This is a 371 of PCT/EP96/00833 filed Mar. 1, 1996.

The invention relates to novel sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents, to a plurality of processes and to novel intermediates for their preparation and to their use as herbicides and fungicides.

Certain sulphonylaminocarbonyltriazolinones are known to have herbicidal properties (cf. EP-A 34148, EP-A 422469, EP-A 425948, EP-A 431291, EP-A 507171). However, the activity of these compounds is not in all aspects satisfactory.

This invention, then, provides sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents of the general formula (I) ##STR2## in which

R¹ represents hydrogen, hydroxyl, amino, alkylideneamino or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl,

R² represents respectively halogen-substituted alkyl or alkenyl, and

R³ represents a respectively optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl,

and salts of the compounds of the formula (I).

The novel sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents of the general formula (I) are obtained when

(a) triazolinones of the general formula (II) ##STR3## in which R¹ and R² are each as defined above

are reacted with sulphonyl isocyanates of the general formula (III)

    R.sup.3 --SO.sub.2 --N═C═O                         (III)

in which

R³ is as defined above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or

(b) triazolinone derivatives of the general formula (IV) ##STR4## in which R¹ and R² are each as defined above, and

Z represents halogen, alkoxy, aralkoxy or aryloxy,

are reacted with sulphonamides of the general formula (V)

    R.sup.3 --SO.sub.2 --NH.sub.2                              (V)

in which

R³ is as defined above,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,

or

(c) triazolinones of the general formula (II) ##STR5## in which R¹ and R² are each as defined above

are reacted with sulphonamide derivatives of the general formula (VI)

    R.sup.3 --SO.sub.2 --NH--CO-Z                              (VI)

in which

R³ is as defined above, and

Z represents halogen, alkoxy, aralkoxy or aryloxy,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,

or

(d) triazolinones of the general formula (II) ##STR6## in which R¹ and R² are each as defined above

are reacted with sulphonyl halides of the general formula (VII)

    R.sup.3 --SO.sub.2 --X                                     (VII)

in which

R³ is as defined above and

X represents halogen

and metal cyanates of the general formula (VIII)

    MOCN                                                       (VIII)

in which

M represents an alkali metal equivalent or an alkaline earth metal equivalent,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

and, if appropriate, the compounds of the formula (I) obtained by process (a), (b), (c) or (d) are converted by customary methods into salts.

The novel sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents of the general formula (I) have a strong herbicidal and/or fungicidal activity.

The invention preferably provides compounds of the formula (I) in which

R¹ represents hydrogen, hydroxyl, amino, C₁ -C₆ -alkylideneamino, optionally fluorine-, chlorine-, bromine-, cyano-, C₁ -C₄ -alkoxy-, C₁ -C₄ -alkyl-carbonyl- or C₁ -C₄ -alkoxy-carbonyl-substituted C₁ -C₆ -alkyl, respectively optionally fluorine-, chlorine- and/or bromine-substituted C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl, respectively optionally fluorine- and/or chlorine-substituted C₁ -C₆ -alkoxy or C₂ -C₆ -alkenyloxy, respectively optionally fluorine- and/or chlorine-substituted C₁ -C₆ -alkylamino, di-(C₁ -C₄ -alkyl)-amino or C₁ -C₄ -alkanoylamino, respectively optionally fluorine-, chlorine-, bromine- and/or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl or C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, or respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁ -C₄ -alkyl-, trifluoromethyl-, C₁ -C₄ -alkoxy- and/or C₁ -C₄ -alkoxy-carbonyl-substituted phenyl or phenyl-C₁ -C₄ -alkyl,

R² represents respectively fluorine-, chlorine- and/or bromine-substituted C₁ -C₆ -alkyl or C₂ -C₆ -alkenyl, and

R³ represents the grouping ##STR7## in which R⁴ and R⁵ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C₁ -C₆ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylamino-carbonyl, di-(C₁ -C₄ -alkyl)-amino-carbonyl, hydroxyl, C₁ -C₄ -alkoxy, formyloxy, C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄ -alkoxy-carbonyloxy, C₁ -C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄ -alkyl)-aminosulphonyl, C₃ -C₆ -cycloalkyl or phenyl), or C₂ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or C₂ -C₆ -alkynyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or C₁ -C₄ -alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or C₁ -C₄ -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or C₂ -C₆ -alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), or C₂ -C₆ -alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₃ -alkylthio or C₁ -C₄ -alkoxycarbonyl), C₃ -C₆ -alkynyloxy, C₃ -C₆ -alkynylthio or the radical --S(O)_(p) --R⁶, where

p represents the numbers 1 or 2, and

R⁶ represents C₁ -C₄ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkylamino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenyl or the radical --NHOR⁷, where

R⁷ represents C₁ -C₁₂ -alkyl (which is optionally substituted by fluorine, chlorine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkylamino-carbonyl or di-(C₁ -C₄ -alkyl)-amino-carbonyl), or C₃ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C₃ -C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl, phenyl-C₁ -C₂ -alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl), or benzhydryl or phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, C₁ -C₂ -fluoroalkoxy, C₁ -C₄ -alkylthio, trifluoromethylthio or C₁ -C₄ -alkoxycarbonyl),

R⁴ and/or R⁵ further represent phenyl or phenoxy, or C₁ -C₄ -alkylcarbonylamino, C₁ -C₄ -alkoxy-carbonylamino, C₁ -C₄ -alkylaminocarbonyl-amino, di-(C₁ -C₄ -alkyl)-amino-carbonylamino, or the radical --CO--R⁸, where

R⁸ represents hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkoxy-C₁ -C₄ -alkylamino or di-(C₁ -C₄ -alkyl)-amino (each of which is optionally substituted by fluorine and/or chlorine),

R⁴ and/or R⁵ further represent trimethylsilyl, thiazolinyl, C₁ -C₄ -alkylsulphonyloxy, di-(C₁ -C₄ -alkyl)-aminosulphonylamino or the radical

    --CH═N--R.sup.9, where

R⁹ represents optionally fluorine-, chlorine-, cyano-, carboxyl-, C₁ -C₄ -alkoxy-, C₁ -C₄ -alkylthio-, C₁ -C₄ -alkylsulphinyl- or C₁ -C₄ -alkylsulphonyl-substituted C₁ -C₆ -alkyl, or optionally fluorine- or chlorine-substituted benzyl, or optionally fluorine- or chlorine-substituted C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl, or optionally fluorine-, chlorine-, bromine-, C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy-, trifluoromethyl-, trifluoromethoxy- or trifluoromethylthio-substituted phenyl, or optionally fluorine- and/or chlorine-substituted C₁ -C₆ -alkoxy, C₃ -C₆ -alkenoxy, C₃ -C₆ -alkinoxy or benzyloxy, or amino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenylamino, C₁ -C₄ -alkylcarbonyl-amino, C₁ -C₄ -alkoxy-carbonylamino, C₁ -C₄ -alkylsulphonylamino or optionally fluorine-, chlorine-, bromine- or methyl-substituted phenylsulphonylamino,

furthermore

R³ represents the radical ##STR8## in which R¹⁰ represents hydrogen or C₁ -C₄ -alkyl,

R¹¹ and R¹² are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C₁ -C₄ -alkoxy-carbonyl, dimethylaminocarbonyl, C₁ -C₄ -alkyl-sulphonyl or di-(C₁ -C₄ -alkyl)-aminosulphonyl;

furthermore

R³ represents the radical ##STR9## in which R¹³ and R¹⁴ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine) or C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine);

furthermore

R³ represents the radical ##STR10## in which R¹⁵ and R¹⁶ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), or C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (each of which are optionally substituted by fluorine and/or chlorine), or aminosulphonyl, mono-(C₁ -C₄ -alkyl)-aminosulphonyl, or di-(C₁ -C₄ -alkyl)-aminosulphonyl or C₁ -C₄ -alkoxy-carbonyl or dimethylaminocarbonyl;

furthermore

R³ represents the radical ##STR11## in which R¹⁷ and R¹⁸ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or bromine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), or C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (each of which are optionally substituted by fluorine and/or chlorine), or di-(C₁ -C₄ -alkyl)-aminosulphonyl;

furthermore

R³ represents the radical ##STR12## in which R¹⁹ and R²⁰ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C₁ -C₄ -alkyl)-aminosulphonyl, C₁ -C₄ -alkoxy-carbonyl or dimethylaminocarbonyl, and

A represents oxygen, sulphur or the grouping N-Z¹, where

Z¹ represents hydrogen, C₁ -C₄ -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C₃ -C₆ -cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-carbonyl or di-(C₁ -C₄ -alkyl)aminocarbonyl;

furthermore

R³ represents the radical ##STR13## in which R²¹ and R²² are identical or different and each represent hydrogen, C₁ -C₄ -alkyl, halogen, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy,

Y¹ represents sulphur or the grouping N--R²³, where

R²³ represents hydrogen or C₁ -C₄ -alkyl;

furthermore

R³ represents the radical ##STR14## in which R²⁴ represents hydrogen, C₁ -C₄ -alkyl, benzyl, pyridyl, quinolyl or phenyl,

R²⁵ represents hydrogen, halogen, cyano, nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C₁ -C₄ -alkoxy-carbonyl, and

R²⁶ represents hydrogen, halogen or C₁ -C₄ -alkyl,

Additionally, the invention preferably provides the sodium, potassium, magnesium, calcium, ammonium, C₁ -C₄ -alkyl-ammonium, di-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-ammonium, tetra-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-sulphonium, C₅ - or C₆ -cycloalkyl-ammonium and di-(C₁ -C₂ -alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which n, R¹, R² and R³ have the preferred meanings given above.

The invention in particular provides compounds of the formula (I) in which

R¹ represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, or represents respectively optionally fluorine- and/or chlorine-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy or butenyloxy, or represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or represents respectively optionally fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, methyl-, trifluoromethyl- or methoxy-substituted benzyl or phenyl,

R² represents fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, and

R³ represents the radical ##STR15## in which R⁴ represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and

R⁵ represents hydrogen, methyl, ethyl, fluorine, chlorine or bromine;

furthermore

R³ represents the radical ##STR16## in which R¹⁰ represents hydrogen,

R¹¹ represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl, and

R¹² represents hydrogen;

furthermore

R³ represents the radical ##STR17## in which R represents methyl, ethyl, n- or i-propyl, or

R³ represents the radical ##STR18## in which R²⁴ represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl,

R²⁵ represents hydrogen, fluorine, chlorine or bromine, and

R²⁶ represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl.

The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the precursors or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, thus including combination between the preferred ranges indicated.

In the definitions of the radicals, hydrocarbon radicals such as alkyl, alkenyl or alkynyl are straight-chain or branched, even in combination with hetero atoms, as in alkoxy, alkylthio or alkylamino, even if this is not explicitly stated.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

Using, for example, 2-trifluoromethoxy-phenylsulphonyl isocyanate and 4-ethyl-5-difluoromethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following equation: ##STR19##

Using, for example, 2-ethylthio-benzenesulphonamide and 2-chlorocarbonyl-4-benzyl-5-(2,2-difluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following equation: ##STR20##

Using, for example, N-methoxycarbonyl-2-methoxy-benzenesulphonamide and 5-(2-chloro-ethoxy)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of the reaction of the process (c) according to the invention can be illustrated by the following equation: ##STR21##

Using, for example, 2-chloro-6-methyl-benzenesulphonyl chloride, 4-allyl-5-(2,3,3-trifluoro-propoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one and sodium cyanate as starting materials, the course of the reaction of the process (d) according to the invention can be illustrated by the following equation: ##STR22##

A general definition of the triazolinones to be used as starting materials in the processes (a), (c) and (d) according to the invention for preparing compounds of the formula (I) is given by the formula (II).

In the formula (II), R¹ and R² each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for R¹ and R².

The triazolinones of the general formula (II) have not been disclosed in the literature; as novel substances, they also form part of the subject matter of the present application.

The novel triazolinones of the formula (II) are obtained when carbazates of the general formula (IX) ##STR23## in which R represents alkyl (preferably methyl or ethyl)

are reacted with diesters of alkyliminocarbonic acid of the general formula (X) ##STR24## in which R¹ and R² are as defined above,

if appropriate in the presence of a diluent such as methanol at temperatures between 0° C. and 100° C. and the thus-formed compounds of the general formula (XI) ##STR25## in which R, R¹ and R² are as defined above

are cyclocondensed--if appropriate after intermediate isolation--if appropriate in the presence of a diluent such as toluene at temperatures between 20° C. and 150° C. (cf. the preparation examples).

The triazolinones of the formula (II) in which R² represents difluoromethyl (R¹ being as defined above) are preferably prepared by reacting urazoles of the general formula (XII) ##STR26## in which R¹ is as defined above

with chlorodifluoromethane in the presence of an acid acceptor such as sodium hydroxide and in the presence of a diluent such as isopropanol and/or water, at temperatures between 0° C. and 100° C. (cf. the preparation examples).

A general definition of the sulphonyl isocyanates also to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I) is given by the formula (III).

In the formula (III), R³ preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for R³.

The starting materials of the formula (III) are known and/or can be prepared by methods known per se (cf. U.S. Pat. No. 4,127,405, U.S. Pat. No. 4,169,719, U.S. Pat. No. 4,371,391, EP-A 7687, EP-A 13480, EP-A 21641, EP-A 23141, EP-A 23422, EP-A 30139, EP-A 35893; EP-A 44808; EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322, EP-A 70041, EP-A 173312).

A general definition of the triazolinone derivatives to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I) is given by the formula (IV). In the formula (IV), R¹ and R² each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R¹ and R² ; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy, phenoxy, halogeno- or nitro-phenoxy, and in particular represents methoxy, phenoxy or 4-nitro-phenoxy.

The starting materials of the formula (IV) have not been disclosed in the literature; as novel substances, they are also part of the subject matter of the present application.

The novel compounds of the formula (IV) are obtained when triazolinones of the general formula (II) ##STR27## in which R¹ and R² are each as defined above,

are reacted with carbonic acid derivatives of the general formula (XIII)

    Z-CO-Z.sup.1                                               (XIII)

in which

Z is as defined above and

Z¹ represents halogen, alkoxy, aralkoxy or aryloxy,

if appropriate in the presence of an acid acceptor, such as, for example, potassium t-butoxide, and if appropriate in the presence of a diluent, such as, for example, tetrahydrofuran or dimethoxyethane, at temperatures between 0° C. and 100° C.

A general definition of the sulphonamides also to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I) is given by the formula (V). In the formula (V), R³ preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R³.

The starting materials of the formula (V) are known and/or can be prepared by methods known per se (cf. U.S. Pat. No. 4,127,405, U.S. Pat. No. 4,169,719, U.S. Pat. No. 4,371,391, EP-A 7687, EP-A 13480, EP-A 21641, EP-A 23141, EP-A 23422, EP-A 30139, EP-A 35893, EP-A 44808, EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322, EP-A 70041, EP-A 173312).

A general definition of the sulphonamide derivatives to be used as starting materials in the process (c) according to the invention for preparing compounds of the formula (I) is given by the formula (VI). In the formula (VI), R³ preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R³ ; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, and in particular represents methoxy or phenoxy.

The starting materials of the formula (VI) are known and/or can be prepared by methods known per se.

A general definition of the sulphonyl halides to be used as starting materials in the process (d) according to the invention for preparing compounds of the formula (I) is given by the formula (VII). In the formula (VII), R³ preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R³ ; X preferably represents fluorine, chlorine or bromine, and in particular represents chlorine.

The starting materials of the formula (VII) are known and/or can be prepared by methods known per se.

The processes (a), (b), (c) and (d) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents in this context are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; esters such as methyl acetate and ethyl acetate; nitriles, for example acetonitrile and propionitrile; amides, for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.

As reaction auxiliaries and/or as acid acceptors in the processes (a), (b), (c) and (d) according to the invention it is possible to employ all acid-binding agents which can customarily be used for such reactions. Preference is given to alkali metal hydroxides, for example sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, for example calcium hydroxide, alkali metal carbonates and alkoxides, such as sodium carbonate and potassium carbonate, sodium tert-butoxide and potassium tert-butoxide, and also basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4,3,0]-non-5-ene (DBN), 1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2,2,2]-octane (DABCO).

The reaction temperatures in the processes (a), (b), (c) and (d) according to the invention can be varied within a relatively wide range. The reactions are in general carried out at temperatures of between -20° C. and +100° C., preferably at temperatures between 0° C. and +80° C.

The processes (a), (b), (c) and (d) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.

For carrying out processes (a), (b), (c) and (d) according to the invention, the starting materials required in each case are in general employed in approximately equimolar quantities. However, it is also possible to use one of the components employed in each case in a relatively large excess. The reactions are in general carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a number of hours at the particular temperature required. Work-up in the case of the processes (a), (b), (c) and (d) according to the invention is in each case carried out by customary methods (cf. the Preparation Examples).

Salts of the compounds of the general formula (I) according to the invention can be prepared if desired. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in an appropriate solvent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding an appropriate base. The salts can then--if desired after prolonged stirring--be isolated by concentration or filtration with suction.

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial crops, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pasture-land, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention are preferably suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both pre-emergence and post-emergence.

Additionally, the active compounds according to the invention have a potent microbicidal action and can be practically employed for controlling undesirable microorganisms. The active compounds are suitable for use as crop protection agents, in particular as fungicides.

Fungicides in plant protection are employed for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides in plant protection are employed for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Some causative organisms of fungal and bacterial diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation:

Xanthomonas species, such as Xanthomonas campestris pv. oryzae;

Pseudomonas species, such as Pseudomonas syringae pv. lachrymans;

Erwinia species, such as Erwinia amylovora;

Pythium species, such as Pythium ultimum;

Phytophthora species, such as Phytophthora infestans;

Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubensis;

Plasmopara species, such as Plasmopara viticola;

Bremia species, such as Bremia lactucae;

Peronospora species, such as Peronospora pisi or P. brassicae;

Erysiphe species, such as Erysiphe graminis;

Sphaerotheca species, such as Sphaerotheca fuliginea;

Podosphaera species, such as Podosphaera leucotricha;

Venturia species, such as Venturia inaequalis;

Pyrenophora species, such as Pyrenophora teres or P. graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as Uromyces appendiculatus;

Puccinia species, such as Puccinia recondita;

Sclerotinia species, such as Sclerotinia sclerotiorum;

Tilletia species, such as Tilletia caries;

Ustilago species, such as Ustilago nuda or Ustilago avenae;

Pellicularia species, such as Pellicularia sasakii;

Pyricularia species, such as Pyricularia oryzae;

Fusarium species, such as Fusarium culmorum;

Botrytis species, such as Botrytis cinerea;

Septoria species, such as Septoria nodorum;

Leptosphaeria species, such as Leptosphaeria nodorum;

Cercospora species, such as Cercospora canescens;

Alternaria species, such as Alternaria brassicae;

Pseudocercosporella species, such as Pseudocercosporella herpotrichoides.

The good toleration, by plants, of the active compounds, at the concentrations required for controlling plant diseases, permits treatment of aerial parts of plants, of vegetative propagation stock and seeds, and of the soil.

The compounds of the formula (I) are particularly suitable for the protective treatment of pomaceous fruit, such as apples, against the causative organism of powdery mildew in apple (Podosphaera leucotricha) and to a certain extent also for use in rice against Pyricularia oryzae.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. Suitable liquid solvents are in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.

Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifying and/or foam-forming agents are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as protein hydrolysates; suitable dispersing agents are: for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, ready-to-use formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for example anilides, such as diflufenican and propanil; arylcarboxylic acids, such as dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxyphenoxy-alkanoic esters, such as diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones, such as chloridazon and norflurazon; carbamates, such as chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides, such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines, such as oryzalin, pendimethalin and trifluralin; diphenyl ethers, such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas, such as chlorotoluron, diuron, fluometuron, isproturon, linuron and methabenzthiazuron; hydroxylamines, such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, such as imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, such as bromoxynil, dichlobenil and ioxynil; oxyacetamides, such as mefenacet; sulphonyl-ureas, such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates, such as butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, such as atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine; triazinones, such as hexazinone, metamitron and metribuzin; others, such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, defenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 2 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

PREPARATION EXAMPLES Example 1 ##STR28## (Process (a))

A solution of 1.9 g (9.5 mmol) of 4-methyl-5-(2,2,2-trifluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one in 50 ml of acetonitrile is mixed with 2.4 g (10 mmol) of 2-methoxycarbonyl-phenylsulphonyl isocyanate, and the mixture is stirred at 20° C. for 12 hours. The mixture is then concentrated under reduced pressure and the residue is crystallized from diethyl ether.

3.7 g (89% of theory) of 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-(2,2,2-trifluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 153° C. are obtained.

Example 2 ##STR29## (Process (b))

3.8 g (12 mmol) of 4-methyl-2-phenoxycarbonyl-5-(2,2,2-trifluoroethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 20 ml of acetonitrile and admixed with 3.4 g (12 mmol) of 2-(N-methoxy-N-methyl-aminosulphonyl)-benzenesulphonamide and 1.9 g (12.5 mmol) of diazabicycloundecene (DBU). After the mixture has been stirred at 20° C. for 1 hour, it is poured into a mixture of methylene chloride/5% strength hydrochloric acid, and the organic phase is separated off, dried with sodium sulphate and concentrated under reduced pressure. The residue is crystallized using diethyl ether.

3.3 g (55% of theory) of 2-[2-(N-methoxy-N-methyl-aminosulphonyl)-phenylsulphonyl-aminocarbonyl]-4-methyl-5-(2,2,2-trifluoroethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 183° C. are obtained.

By the methods of Examples 1 and 2 and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, for example, the compounds of the formula (I) listed in Table 1 below. ##STR30##

                                      TABLE 1                                      __________________________________________________________________________     Examples of compounds of the formula (I)                                       Ex.                                  Melting                                   No.                                                                               R.sup.1 R.sup.2  R.sup.3          point (° C.)                       __________________________________________________________________________     3  CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                                        168                                       4  CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR31##       189                                       5  CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR32##       135                                       6  CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR33##       159                                       7  CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR34##       178                                       8  CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR35##       144                                       9  CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR36##       119                                       10 CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR37##       120                                       11 CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR38##       203                                       12 CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR39##       193                                       13 CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR40##       144                                       14 CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR41##       180                                       15 CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR42##       162                                       16 CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR43##       216                                       17 CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                        ##STR44##       102                                       18 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR45##       129                                       19 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR46##       122                                       20 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR47##       153                                       21 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR48##       140                                       22 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR49##       146                                       23 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR50##       148                                       24 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR51##       145                                       25 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR52##       142                                       26 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR53##       155                                       27 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR54##       136                                       28 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR55##       158                                       29 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR56##       153                                       30 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR57##       150                                       31 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR58##       160                                       32 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR59##       196                                       33 CH.sub.3                                                                               CH.sub.2 CCl.sub.3                                                                       ##STR60##       182                                       34 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR61##       120                                       35 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR62##       116                                       36 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR63##       163                                       37 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR64##       154                                       38 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR65##       126                                       39 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR66##       109                                       40 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR67##       160                                       41 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR68##       153                                       42 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR69##       163                                       43 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR70##       150                                       44 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR71##       159                                       45 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR72##       168                                       46 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR73##       163                                       47 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR74##       117                                       48 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR75##       142                                       49 CH.sub.3                                                                               CH.sub.2 --CF.sub.2 --CHF.sub.2                                                          ##STR76##       154                                       50 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR77##       96                                        51 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR78##       117                                       52 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR79##       108                                       53 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR80##       133                                       54 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR81##       152                                       55 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR82##       117                                       56 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR83##       148                                       57 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR84##       108                                       58 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR85##       119                                       59 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR86##       89                                        60 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR87##       140                                       61 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR88##       127                                       62 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR89##       120                                       63 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR90##       143                                       64 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR91##       141                                       65 C.sub.2 H.sub.5                                                                        CH.sub.2 --CF.sub.3                                                                      ##STR92##       152                                       66 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR93##       125                                       67 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR94##       86                                        68 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR95##       108                                       69 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR96##       93                                        70 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR97##       162                                       71 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR98##       103                                       72 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR99##       144                                       73 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR100##      110                                       74 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR101##      115                                       75 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR102##      126                                       76 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR103##      118                                       77 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR104##      104                                       78 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR105##      128                                       79 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR106##      119                                       80 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR107##      123                                       81 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR108##      .sup.1 H--NMR  (CDCl.sub.3,                                                    δ):  2.52(s,  SCH.sub.3), 6.13                                            (q, CH.sub.2 --  CF.sub.3) ppm           82 CH.sub.2 --CH═CH.sub.2                                                             CH.sub.2 --CF.sub.3                                                                      ##STR109##                                                83                                                                                 ##STR110##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR111##      108                                       84                                                                                 ##STR112##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR113##      132                                       85                                                                                 ##STR114##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR115##      124                                       86                                                                                 ##STR116##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR117##      120                                       87                                                                                 ##STR118##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR119##      .sup.1 H--NMR  (CDCl.sub.3,                                                    δ):  4.74  (q, CH.sub.2                                                  CF.sub.3),  6.66(t,  OCHF.sub.2),                                              ppm                                       88                                                                                 ##STR120##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR121##      154                                       89                                                                                 ##STR122##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR123##      158                                       90                                                                                 ##STR124##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR125##      141                                       91                                                                                 ##STR126##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR127##      121                                       92                                                                                 ##STR128##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR129##      119                                       93                                                                                 ##STR130##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR131##      116                                       94                                                                                 ##STR132##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR133##      114                                       95                                                                                 ##STR134##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR135##      143                                       96                                                                                 ##STR136##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR137##      174                                       97                                                                                 ##STR138##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR139##      154                                       98                                                                                 ##STR140##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR141##      117                                       99                                                                                 ##STR142##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR143##      175                                       100                                                                               CH.sub.3                                                                               CHF.sub.2                                                                                ##STR144##      178                                       101                                                                               CH.sub.3                                                                               CHF.sub.2                                                                                ##STR145##      189                                       102                                                                               CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                      ##STR146##      142                                       103                                                                               CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                      ##STR147##      55                                        104                                                                               CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                      ##STR148##      127                                       105                                                                               CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                      ##STR149##      128                                       106                                                                                ##STR150##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR151##      118                                       107                                                                               CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                      ##STR152##      121                                       108                                                                               CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                      ##STR153##      118                                       109                                                                                ##STR154##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR155##      79                                        110                                                                               CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                      ##STR156##      94                                        111                                                                                ##STR157##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR158##      105                                       112                                                                               CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                      ##STR159##      182                                       113                                                                                ##STR160##                                                                            CH.sub.2 --CF.sub.3                                                                      ##STR161##      154                                       114                                                                                ##STR162##                                                                            CH.sub.2 CF.sub.3                                                                        ##STR163##      154                                       115                                                                               CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                      ##STR164##      167                                       __________________________________________________________________________

Starting materials of the formula (II):

Example (II-1) ##STR165## Step 1: Dibutyltin bis-2,2,3,3-tetrafluoropropoxide

723 g (2.45 mol) of dibutyltin dimethoxide with 777 g (5.89 mol) of 2,2,3,3-tetrafluoro-propanol are heated to 120° C. under nitrogen. Most of the methanol liberated in this process is distilled off over a column. The remaining methanol and excess 2,2,3,3-tetrafluoro-propanol are then substantially removed under water pump vacuum (about 15 mbar), the dibutyltin bis-2,2,3,3-tetrafluoropropoxide remaining as residue.

Step 2: Bis-(2,2,3,3-tetrafluoropropyl) methyliminocarbonate

At 40° C., 175 g (2.39 mol) of methyl isothiocyanate are added dropwise to dibutyltin bis-2,2,3,3-tetrafluoropropoxide obtained as described above, and the mixture is then heated under nitrogen to 120° C. for 36 hours. The mixture is then subjected to a crude distillation, first under water pump vacuum and then under oil pump vacuum (final temperature in the bottom: 170° C. at 1 mbar). Rectification under oil pump vacuum affords 555 g (77% of theory) of bis-(2,2,3,3-tetrafluoropropyl) methyliminocarbonate.

Boiling point: 73° C. (15 mbar), purity: 98.3%

Step 3: 4-Methyl-5-(2,2,3,3-tetrafluoro-propoxy)-2,4-dihydro-3H-1,2,4-triazol-3-on

555 g (1.83 mol) of bis-(2,2,3,3-tetrafluoropropyl) methyliminocarbonate are dissolved in 500 ml of tetrahydrofuran and, with ice cooling (0° C. to 5° C.), admixed with 18.7 g (183 mmol) of pivalic acid (catalyst) and 278 g (1.83 mol) of phenyl carbazate. The mixture is stirred for 2 hours at 20° C. and then warmed to 50° C., resulting in a crystal pulp that can be stirred only with difficulty. When this is heated to 80° C., the solution becomes homogeneous again. First, at about 200 mbar, most of the tetrahydrofuran and then, at about 15 mbar, most of the 2,2,3,3-tetrafluoro-propanol and phenol are distilled off. The residue is then freed of the remaining volatile components at a head temperature of 130° C. and a pressure of about 0.5 mbar and then taken up in 400 ml of hot toluene. After cooling to 0° C., the crystalline product is isolated by filtration under suction.

280 g (67% of theory) of 4-methyl-5-(2,2,3,3-tetrafluoro-propoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 101° C. are obtained.

Example (II-2) ##STR166##

11.85 g (0.10 mol) of 4-methylurazole are dissolved in a mixture of 100 ml of isopropanol, 25 ml of water and 12 g of 45% strength aqueous sodium hydroxide solution (0.30 mol of NaOH). At 40° C., difluorochloromethane (Frigen 22) is slowly passed through with stirring. After 27.7 g (0.41 mol) have been passed through, the reaction is interrupted and the reaction mixture is cooled. The isopropanol phase is separated off and concentrated under reduced pressure. The residue is stirred with diethyl ether and insoluble components are filtered off. The ether phase is concentrated under reduced pressure and the residue that remains is purified by preparative layer chromatography (eluent methylene chloride/methanol=20/3).

0.9 g (5.5% of theory) of 5-difluoromethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 111° C. is obtained.

By the methods of Examples (II-1) and (II-2), it is also possible to prepare, for example, the compounds of the formula (II) listed in Table 2 below. ##STR167##

                  TABLE 2                                                          ______________________________________                                         Examples of compounds of the formula (II)                                      Ex.                            Melting                                         No.  R.sup.1      R.sup.2      point (° C.)                             ______________________________________                                         II-1 CH.sub.3     CH.sub.2 CF.sub.3                                                                           128                                             II-4 CH.sub.3     CH.sub.2 CCl.sub.3                                                                          139                                             II-5 CH.sub.3     CH.sub.2 --CF.sub.2 --CHF.sub.2                                                             101                                             II-6 C.sub.2 H.sub.5                                                                             CH.sub.2 --CF.sub.3                                                                         95                                              II-7 CH.sub.2 --CH═CH.sub.2                                                                  CH.sub.2 --CF.sub.3                                                                         62                                              II-8                                                                                             CH.sub.2 --CF.sub.3                                                                         113                                             II-9                                                                                 ##STR168##  CH.sub.2 --CF.sub.3                                          II-10                                                                                ##STR169##  CHF.sub.2                                                    II-11                                                                               C.sub.2 H.sub.5                                                                             CHF.sub.2                                                    II-12                                                                               CH.sub.2 --CH═CH.sub.2                                                                  CHF.sub.2                                                    II-13                                                                                ##STR170##  CHF.sub.2                                                    II-14                                                                               CH.sub.3     CH(CF.sub.3).sub.2                                           II-15                                                                               C.sub.2 H.sub.5                                                                             CH(CF.sub.3).sub.2                                           II-16                                                                               CH.sub.2 --CH═CH.sub.2                                                                  CH(CF.sub.3).sub.2                                           II-17                                                                                ##STR171##  CH(CF.sub.3).sub.2                                           II-18                                                                                ##STR172##  CH(CF.sub.3).sub.2                                           II-19                                                                               CH.sub.3     CH.sub.2 --CH.sub.2 --F                                      II-20                                                                               C.sub.2 H.sub.5                                                                             CH.sub.2 --CH.sub.2 --F                                      II-21                                                                               CH.sub.2 --CH═CH.sub.2                                                                  CH.sub.2 --CH.sub.2 --F                                      II-22                                                                                ##STR173##  CH.sub.2 --CH.sub.2 --F                                      II-23                                                                                ##STR174##  CH.sub.2 --CH.sub.2 --F                                      II-24                                                                               NH.sub.2     CH.sub.2 --CH.sub.2 --F                                      II-25                                                                               NH--CH.sub.3 CH.sub.2 --CH.sub.2 --F                                      II-26                                                                               N(CH.sub.3).sub.2                                                                           CH.sub.2 --CH.sub.2 --F                                      II-27                                                                               NH.sub.2     CH.sub.2 --CF.sub.3                                          II-28                                                                               NH--CH.sub.3 CH.sub.2 --CF.sub.3                                          II-29                                                                               N(CH.sub.3).sub.2                                                                           CH.sub.2 --CF.sub.3                                          II-30                                                                               NH.sub.2     CHF.sub.2                                                    II-31                                                                               NH--CH.sub.3 CHF.sub.2                                                    II-32                                                                               N(CH.sub.3).sub.2                                                                           CHF.sub.2                                                    II-33                                                                               CH.sub.3     CH.sub.2 --CHF.sub.2                                         II-34                                                                               C.sub.2 H.sub.5                                                                             CH.sub.2 --CHF.sub.2                                         II-35                                                                               CH.sub.2 --CH═CH.sub.2                                                                  CH.sub.2 --CHF.sub.2                                         II-36                                                                                ##STR175##  CH.sub.2 --CHF.sub.2                                         II-37                                                                                ##STR176##  CH.sub.2 --CHF.sub.2                                         ______________________________________                                    

Starting materials of the formula (IV):

Example (IV-1) ##STR177##

At 20° C., 51.7 g (0.33 mol) of phenyl chloroformate are added dropwise with efficient stirring to a mixture of 59.1 g (0.30 mol) of 4-methyl-5-(2,2,2-trifluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one, 100 ml of water, 400 ml of methylene chloride, 13.2 g (0.33 mol) of sodium hydroxide and 1.0 g of tetrabutylammonium bromide. After the addition, stirring is continued for a further 16 hours and the organic phase is then separated off, washed with water, dried and concentrated. The residue is crystallized from diisopropyl ether.

87.6 g (92% of theory) of 4-methyl-2-phenoxycarbonyl-5-(2,2,2-trifluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 105° C. are obtained.

By the method of Example (IV-1) it is also possible to prepare, for example, the compounds of the formula (IV) listed in Table 3 below.

                  TABLE 3                                                          ______________________________________                                         Examples of compounds of the formula (IV)                                      Ex.                                  Melting                                   No.  R.sup.1     R.sup.2      Z      point (° C.)                       ______________________________________                                         IV-2                                                                                 ##STR178## CH.sub.2 --CF.sub.3                                                                         O--C.sub.6 H.sub.5                                                                    91                                        IV-3 C.sub.2 H.sub.5                                                                            CH.sub.2 --CF.sub.3                                                                         O--C.sub.6 H.sub.5                               IV-4 CH.sub.2 --CH═CH.sub.2                                                                 CH.sub.2 --CF.sub.3                                                                         O--C.sub.6 H.sub.5                               IV-5 CH.sub.3    CH.sub.2 CCl.sub.3                                                                          O--C.sub.6 H.sub.5                               IV-6 C.sub.2 H.sub.5                                                                            CH.sub.2 CCl.sub.3                                                                          O--C.sub.6 H.sub.5                               IV-7 CH.sub.2 --CH═CH.sub.2                                                                 CH.sub.2 CCl.sub.3                                                                          O--C.sub.6 H.sub.5                               IV-8                                                                                 ##STR179## CH.sub.2 CCl.sub.3                                                                          O--C.sub.6 H.sub.5                               IV-9                                                                                 ##STR180## CH.sub.2 CCl.sub.3                                                                          O--C.sub.6 H.sub.5                               IV-10                                                                                ##STR181## CH.sub.2 --CF.sub.3                                                                         O--C.sub.6 H.sub.5                               IV-11                                                                               NH.sub.2    CH.sub.2 --CF.sub.3                                                                         O--C.sub.6 H.sub.5                               IV-12                                                                               NH--CH.sub.3                                                                               CH.sub.2 --CF.sub.3                                                                         O--C.sub.6 H.sub.5                               IV-13                                                                               N(CH.sub.3).sub.2                                                                          CH.sub.2 --CF.sub.3                                                                         O--C.sub.6 H.sub.5                               IV-14                                                                               CH.sub.3    CH.sub.2 --CF.sub.2 --CHF.sub.2                                                             O--C.sub.6 H.sub.5                               IV-15                                                                               C.sub.2 H.sub.5                                                                            CH.sub.2 --CF.sub.2 --CHF.sub.2                                                             O--C.sub.6 H.sub.5                               IV-16                                                                               CH.sub.2 --CH═CH.sub.2                                                                 CH.sub.2 --CF.sub.2 --CHF.sub.2                                                             O--C.sub.6 H.sub.5                               IV-17                                                                                ##STR182## CH.sub.2 --CF.sub.2 --CHF.sub.2                                                             O--C.sub.6 H.sub.5                               IV-18                                                                                ##STR183## CH.sub.2 --CF.sub.2 --CHF.sub.2                                                             O--C.sub.6 H.sub.5                               IV-19                                                                               N(CH.sub.3).sub.2                                                                          CH.sub.2 --CF.sub.2 --CHF.sub.2                                                             O--C.sub.6 H.sub.5                               ______________________________________                                    

USE EXAMPLES Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, the soil is watered with the preparation of the active compound. It is advantageous to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, the compounds according to Preparation Examples 1, 2, 3, 4, 5, 6, 9, 11, 12, 15, 16, 17, 25, 50, 54, 66, 83, 84, 85, 86, 87, 88, 89, 91, 93, 94, 95, 96, 97, 98, 99, 100 and 101, for example, exhibit a strong action against weeds.

                                      TABLE A                                      __________________________________________________________________________     Pre-emergence test/greenhouse                                                  Compound of                                                                    Preparation                                                                           Applica-                                                                Example                                                                               tion rate                                                                           Bro-                                                                              Lo-   Ama-                                                                               Galin-                                                                             Matri-                                                                             Sina-                                                                             Sola-                                      No.    (g/ha)                                                                              mus                                                                               lium                                                                              Poa                                                                               ranthus                                                                            soga                                                                               caria                                                                              pis                                                                               num                                        __________________________________________________________________________     83     125  95 95 95 90  95  90  90 95                                         84     125  90 90 90 90  95  90  90 95                                         85     125  90 95 90 90  95  95  90 95                                         86     125  95 80 90 90  95  95  95 95                                          1     125  95 95 95 90  90  90  80 95                                          3     125  95 90 80 80  70  95  80 90                                          4     125  95 95 95 95  95  90  95 95                                          5     125  95 -- 80 95  95  95  95 95                                          6     125  95 50 95 95  70  60  90 95                                         50     125  95 90 90 90  80  90  90 90                                         54     125  95 90 90 90  95  90  70 90                                         87     125  90 90 90 90  70  50  80 90                                         88     125  90 90 90 80  95  95  80 90                                         89     125  90 80 80 90  95  95  80 90                                         91     125  90 70 80 80  80  70  80 90                                          9     125  95 95 95 95  95  100 80 95                                         11     125  -- 60 50 90  100 100 80 70                                         12     125  80 80 80 95  100 80  80 80                                         15     125  95 -- 60 95  70  95  90 90                                         16     125  80 90 95 95  60  80  90 90                                         93     125  95 95 95 95  95  95  95 95                                         94     125  90 90 90 80  95  90  80 90                                         95     125  80 90 -- 90  95  90  90 90                                         96     125  95 95 90 90  90  90  90 80                                         97     250  95 95 90 95  95  95  90 95                                          2     250  95 95 95 95  95  80  80 95                                         17     125  95 70 80 90  90  90  80 90                                         98     125  90 70 80 90  90  80  80 90                                         25     125  -- -- 90 60  100 95  90 70                                         66     125  90 95 90 70  95  95  70 95                                         99     125  90 90 95 100 70  50  90 90                                         100    125  -- 95 95 50  --  70  80 95                                         101    125  70 95 90 90  80  50  80 90                                         __________________________________________________________________________

Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compounds desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compounds desired are employed in 2000 l of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, the compounds of Preparation Examples 1, 2, 4, 5, 9, 16, 17, 25, 50, 66, 83, 84, 85, 86, 87, 88, 89, 93, 94, 95, 96, 98, 99 and 100 show a strong action against weeds.

                                      TABLE B                                      __________________________________________________________________________     Post-emergence test/greenhouse                                                 Compound                                                                       of    Applic-                                                                  Preparation                                                                          ation                                                                    Example                                                                              rate                                                                               Alope-  Lo-                                                                               Ama-        Heli-                                                                              Sola-                                                                             Vero-                                  No.   (g/ha)                                                                             curus                                                                              Avena                                                                              lium                                                                              ranthus                                                                            Datura                                                                             Galium                                                                             anthus                                                                             num                                                                               nica                                   __________________________________________________________________________     83    250 90  90  95 90  90  90  90  90 90                                     84    250 --  95  70 70  90  80  90  90 95                                     85    250 --  --  95 70  90  90  90  80 95                                     86    500 --  80  90 100 90  90  100 95 100                                     1    250 90  90  100                                                                               80  80  70  90  90 95                                      4    250 90  70  90 80  90  70  90  90 90                                      5    250 80  50  -- 95  90  70  95  90 100                                    87    125 70  80  50 80  95  70  80  90 90                                     50     60 80  50  80 95  50  85  --  90 70                                     88    250 80  --  70 95  95  90  100 90 90                                     89    125 50  --  80 95  95  90  95  95 95                                      9     60 100 95  80 95  90  90  80  95 90                                     16    125 --  50  70 95  80  50  100 95 70                                     93    125 95  90  80 95  95  90  100 95 70                                     94    125 80  90  80 70  90  70  80  90 --                                     95     60 70  70  -- 90  --  95  70  70 80                                     17    125 50  --  -- 90  80  50  100 95 90                                     98    125 --  --  -- 95  50  --  100 80 90                                     96     60 95  70  90 95  70  90  80  -- 50                                      2    125 60  60  50 80  80  --  95  80 80                                     25     60 60  50  -- 80  80  50  100 90 --                                     66     60 50  --  -- 80  80  50  100 90 --                                     99     60 60  50  50 90  95  95  60  90 70                                     100   125 --  90  80 90  90  90  --  95 90                                     __________________________________________________________________________

Example C

Podosphaera test (apple)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated quantities of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound. After the spray coating has dried on, the plants are inoculated by dusting with conidiae of the causative organism of apple mildew (Podosphaera leucotricha).

The plants are then placed in a greenhouse at 23° C. and a relative atmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation.

In this test, the compounds of Preparation Examples 1, 3, 83 and 85, for example, have an efficacy of 87 to 100% at an active compound concentration of 25 ppm.

                  TABLE C                                                          ______________________________________                                         Podosphaera test (apple)/protective                                                              Efficacy in % of the untreated                               Active compound (compound of                                                                        control at an active compound                             Preparation Example No.)                                                                                concentration of 25 ppm                               ______________________________________                                                 1         89                                                            3                                                87                           83                                               100                           85                                               99                            ______________________________________                                    

Example D

Sphaerotheca test (cucumber)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated quantities of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound. After the spray coating has dried on, the plants are dusted with conidiae of the fungus Sphaerotheca fuliginea.

The plants are then placed in a greenhouse at 23 to 24° C. and at a relative atmospheric humidity of about 75%.

Evaluation is carried out 10 days after the inoculation.

In this test, the compound of Preparation Example 50, for example, has an efficacy of 92% at an active compound concentration of 100 ppm.

                  TABLE D                                                          ______________________________________                                         Sphaerotheca test (cucumber)/protective                                                          Efficacy in % of the untreated                                                      control at an active compound                           Active compound (compound of                                                                                                       concentration              Preparation Example No.)                                                                                  of 100 ppm                                          ______________________________________                                         50                92                                                           ______________________________________                                     

What is claimed is:
 1. A compound of the formula (I) ##STR184## wherein R¹ represents methyl or cyclopropyl,R² represents --CH₂ --CF₃, R³ represents the grouping ##STR185## in which R⁴ and R⁵ are identical or different and each represent chlorine, bromine, C₁ -C₆ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, or C₁ -C₄ -alkoxy (which is optionally substituted by fluorine, chlorine, bromine), or C₁ -C₄ -alkylthio, or C₂ -C₆ -alkenyloxy, or C₃ -C₆ -alkynyloxy, or the radical --S(O)_(p) --R⁶, wherep represents the number 2, and R⁶ represents C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy-C₁ -C₄ -alkylamino, R⁴ and/or R⁵ further represent the radical CO--R⁸, whereR⁸ represents C₁ -C₆ -alkoxy, R⁴ and/or R⁵ further represent C₁ -C₄ -alkyl-sulphonyloxy, or their sodium, potassium, magnesium, calcium, ammonium, C₁ -C₄ -alkyl-ammonium, di-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-ammonium, tetra-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-sulphonium, C₅ - or C₆ -cycloalkyl-ammonium and di-(C₁ -C₂ -alkyl)-benzyl-ammonium salt with the proviso that the compound of the following structure is excluded ##STR186##
 2. A compound of the formula (I) or salt thereof according to claim 1 wherein R¹ represents methyl or cyclopropyl,R² represents CH₂ --CF₃, R³ represents the radical ##STR187## in which R⁴ represents chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphonyl, ethylsulphonyl, N-methoxy-N-methylaminosulphonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, andR⁵ represents methyl, ethyl, fluorine, with the proviso that the compound of the following structure is excluded ##STR188##
 3. A compound, 2-(2-ethoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-(2,2,2-trifluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one having the structural formula:
 4. An herbicidal composition comprising an herbicidally effective amount of a compound according to claim 1 and a carrier.
 5. A method of controlling unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation an herbicidally effective amount of a compound according to claim
 1. 